EP4082519A9 - Dendrobium officinale oligosaccharide and derivative thereof, and preparation methods therefor and applications thereof - Google Patents
Dendrobium officinale oligosaccharide and derivative thereof, and preparation methods therefor and applications thereof Download PDFInfo
- Publication number
- EP4082519A9 EP4082519A9 EP21876726.7A EP21876726A EP4082519A9 EP 4082519 A9 EP4082519 A9 EP 4082519A9 EP 21876726 A EP21876726 A EP 21876726A EP 4082519 A9 EP4082519 A9 EP 4082519A9
- Authority
- EP
- European Patent Office
- Prior art keywords
- dendrobium officinale
- oligosaccharide
- water
- residue
- dendrobium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 241001076416 Dendrobium tosaense Species 0.000 title claims abstract description 252
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 182
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 182
- 238000002360 preparation method Methods 0.000 title claims abstract description 39
- 230000002519 immonomodulatory effect Effects 0.000 claims abstract description 31
- 230000003712 anti-aging effect Effects 0.000 claims abstract description 30
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 12
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 10
- 235000013305 food Nutrition 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 107
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000000284 extract Substances 0.000 claims description 35
- 150000004676 glycans Chemical class 0.000 claims description 29
- 229920001282 polysaccharide Polymers 0.000 claims description 29
- 239000005017 polysaccharide Substances 0.000 claims description 29
- 239000006071 cream Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 24
- 239000011550 stock solution Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 235000011187 glycerol Nutrition 0.000 claims description 20
- 229920002125 Sokalan® Polymers 0.000 claims description 18
- 239000008367 deionised water Substances 0.000 claims description 18
- 229910021641 deionized water Inorganic materials 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 18
- -1 C1-C18 alkyl carboxylic acid Chemical class 0.000 claims description 16
- 230000008439 repair process Effects 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 239000002244 precipitate Substances 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 14
- 229960001631 carbomer Drugs 0.000 claims description 14
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 14
- 239000006210 lotion Substances 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 13
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 12
- 239000002537 cosmetic Substances 0.000 claims description 12
- 239000000839 emulsion Substances 0.000 claims description 12
- 150000002191 fatty alcohols Chemical class 0.000 claims description 12
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 12
- 238000005119 centrifugation Methods 0.000 claims description 11
- 108010059892 Cellulase Proteins 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 229940106157 cellulase Drugs 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 150000002338 glycosides Chemical group 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 8
- 235000021355 Stearic acid Nutrition 0.000 claims description 8
- ZPUKPAPWEWUPTC-UHFFFAOYSA-N ethyl 4-ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(CC)C=C1 ZPUKPAPWEWUPTC-UHFFFAOYSA-N 0.000 claims description 8
- 238000006206 glycosylation reaction Methods 0.000 claims description 8
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims description 8
- 229940057995 liquid paraffin Drugs 0.000 claims description 8
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 8
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N palmityl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 8
- 230000002335 preservative effect Effects 0.000 claims description 8
- 239000008117 stearic acid Substances 0.000 claims description 8
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 claims description 7
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 7
- 239000006228 supernatant Substances 0.000 claims description 7
- 239000000341 volatile oil Substances 0.000 claims description 7
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 6
- 238000007873 sieving Methods 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 4
- XULHFMYCBKQGEE-MRXNPFEDSA-N 2-Hexyl-1-decanol Natural products CCCCCCCC[C@H](CO)CCCCCC XULHFMYCBKQGEE-MRXNPFEDSA-N 0.000 claims description 4
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 claims description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 4
- 239000004166 Lanolin Substances 0.000 claims description 4
- 229960000271 arbutin Drugs 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
- 229960000541 cetyl alcohol Drugs 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 230000013595 glycosylation Effects 0.000 claims description 4
- XQSBLCWFZRTIEO-UHFFFAOYSA-N hexadecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[NH3+] XQSBLCWFZRTIEO-UHFFFAOYSA-N 0.000 claims description 4
- 230000000415 inactivating effect Effects 0.000 claims description 4
- 229940039717 lanolin Drugs 0.000 claims description 4
- 235000019388 lanolin Nutrition 0.000 claims description 4
- BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 239000011675 vitamin B5 Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 230000001279 glycosylating effect Effects 0.000 claims description 3
- 230000002779 inactivation Effects 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000002390 rotary evaporation Methods 0.000 claims description 3
- 230000003544 deproteinization Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 23
- 102000029816 Collagenase Human genes 0.000 abstract description 14
- 108060005980 Collagenase Proteins 0.000 abstract description 14
- 229960002424 collagenase Drugs 0.000 abstract description 14
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 abstract description 10
- 108090001005 Interleukin-6 Proteins 0.000 abstract description 10
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 10
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract description 10
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
- 125000003563 glycoside group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 230000028327 secretion Effects 0.000 description 16
- 239000000523 sample Substances 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 230000005764 inhibitory process Effects 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- 102000016387 Pancreatic elastase Human genes 0.000 description 12
- 108010067372 Pancreatic elastase Proteins 0.000 description 12
- 239000007853 buffer solution Substances 0.000 description 12
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 11
- 229920002674 hyaluronan Polymers 0.000 description 11
- 229960003160 hyaluronic acid Drugs 0.000 description 11
- 102000035195 Peptidases Human genes 0.000 description 10
- 108091005804 Peptidases Proteins 0.000 description 10
- 239000004365 Protease Substances 0.000 description 10
- 210000003491 skin Anatomy 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 102000004889 Interleukin-6 Human genes 0.000 description 9
- 239000013641 positive control Substances 0.000 description 9
- 230000032683 aging Effects 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000002158 endotoxin Substances 0.000 description 8
- 229920006008 lipopolysaccharide Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 230000003064 anti-oxidating effect Effects 0.000 description 6
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000002000 scavenging effect Effects 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 238000008157 ELISA kit Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- AIGAZQPHXLWMOJ-UHFFFAOYSA-N Tanshinone I Chemical compound C1=CC2=C(C)C=CC=C2C(C(=O)C2=O)=C1C1=C2C(C)=CO1 AIGAZQPHXLWMOJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 2
- 235000005487 catechin Nutrition 0.000 description 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000105 evaporative light scattering detection Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 210000004927 skin cell Anatomy 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 description 1
- YMMPZCZOLKBHAP-IHPCNDPISA-N (2s)-2-[[(2s)-1-[2-[[2-[[(2s)-1-[2-(phenylmethoxycarbonylamino)acetyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)CNC(=O)[C@H]1N(C(=O)CNC(=O)OCC=2C=CC=CC=2)CCC1 YMMPZCZOLKBHAP-IHPCNDPISA-N 0.000 description 1
- 241001523681 Dendrobium Species 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229930183118 Tanshinone Natural products 0.000 description 1
- 102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
- 108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007640 basal medium Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012679 serum free medium Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0087—Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/898—Orchidaceae (Orchid family)
- A61K36/8984—Dendrobium
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0288—Applications, solvents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D21/00—Separation of suspended solid particles from liquids by sedimentation
- B01D21/26—Separation of sediment aided by centrifugal force or centripetal force
- B01D21/262—Separation of sediment aided by centrifugal force or centripetal force by using a centrifuge
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0033—Xanthan, i.e. D-glucose, D-mannose and D-glucuronic acid units, saubstituted with acetate and pyruvate, with a main chain of (beta-1,4)-D-glucose units; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/318—Foods, ingredients or supplements having a functional effect on health having an effect on skin health and hair or coat
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/324—Foods, ingredients or supplements having a functional effect on health having an effect on the immune system
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/50—Polysaccharides, gums
- A23V2250/51—Polysaccharide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present disclosure relates to the technical field of natural medicine chemistry, and in particular to a Dendrobium officinale oligosaccharide, a Dendrobium officinale oligosaccharide derivative and a preparation method and use thereof.
- Dendrobium officinale ( Dendrobium officinale Kimura et Migo ) is a perennial herb of the genus Dendrobium in the family Orchidaceae, which is listed in each edition of the Pharmacopoeia. According to the records in the Pharmacopoeia, it has the effects of such as engendering liquid and nourishing stomach, nourishing yin and clearing heat, moistening lung and boosting kidney, and brightening eyes and strengthening lumbus. Modern pharmacological research shows that Dendrobium officinale has antioxidative, hypoglycemic, immunomodulatory and anti-inflammatory activities. It is recorded in ancient literatures that the stem of Dendrobium officinale can be used for moisturizing skin and treating diabetes. Studies have shown that Dendrobium officinale mainly contains polysaccharides, stilbene, flavonoids, phenanthrene, lignin and other chemical components.
- Physiological aging refers to the physiological degeneration process that occurs after the mature period
- pathological aging is the senility changes caused by various external factors (including various diseases). The two are actually difficult to distinguish. It is recorded in ancient literatures that Dendrobium officinale has the anti-aging effects, and the natural, green, safe and efficient anti-aging substances in Dendrobium officinale are thus the focus of research.
- Dendrobium officinale At present, many domestic and foreign researchers have conducted research on the extraction and separation of chemical components in various parts of Dendrobium officinale. Most of the researchers mainly obtain small-molecule phenol components or polysaccharides with a molecular weight of more than 100,000. Some researchers have isolated 20 compounds from Dendrobium officinale, mainly bibenzil components, and have found that the small-molecule phenol components of Dendrobium officinale have antioxidative, anti-inflammatory and anti-tumor effects through activity screening. Some researchers have extracted and separated two polysaccharides from Dendrobium officinale with a molecular weight of 7.4 ⁇ 10 5 Da and 5.4 ⁇ 10 5 Da, respectively.
- Some researchers have used a method of water extraction, alcohol precipitation and sulfuric acid hydrolysis to obtain polysaccharides from Dendrobium officinale, and have found that the polysaccharides of Dendrobium officinale influence the count of peripheral white blood cells in mice through activity screening, indicating an immunomodulatory effect.
- Some researchers have obtained polysaccharides from Dendrobium officinale by ultrasonic extraction and have found that the polysaccharides of Dendrobium officinale influence the SOD, MDA and CAT of Drosophila through activity screening, indicating an antioxidative activity.
- the present disclosure provides a Dendrobium officinale oligosaccharide, a Dendrobium officinale oligosaccharide derivative and a preparation method and use thereof. It is illustrated that the Dendrobium officinale oligosaccharide has anti-aging and immunomodulatory effects, and is suitable for applying to skin cosmetics, health foods and medicines with anti-aging and immunomodulatory effects.
- the present disclosure mainly provides the following technical solutions:
- the present disclosure provides a Dendrobium officinale oligosaccharide, comprising 3-9 glycoside residues and a glucose residue at a non-reducing end.
- the Dendrobium officinale oligosaccharide comprises 6 glycoside residues.
- the Dendrobium officinale oligosaccharide has a structure represented by formula (I):
- the glycoside residue includes a galactose residue, a mannose residue and a glucose residue.
- a molar ratio of the galactose residue, the mannose residue and the glucose residue is (3-2) : (2-1) : (2-1).
- a molar ratio of the galactose residue, the mannose residue and the glucose residue is 2 : 1 : 1.
- the present disclosure provides a Dendrobium officinale oligosaccharide derivative, where the Dendrobium officinale oligosaccharide derivative is generated by reacting the glucose residue of the Dendrobium officinale oligosaccharide according to the above technical solutions with a hydrophobic residue, and the hydrophobic residue includes any one of linear or branched C 1 -C 18 alkyl, C 1 -C 18 alkyl carboxylic acid, C 1 -C 18 alkyl amine, C 1 -C 18 aryl alkyl and C 1 -C 18 alkyl amide, or the hydrophobic residue includes any one of benzoyl, phenylacetyl and phenylpropionyl.
- the present disclosure provides use of the Dendrobium officinale oligosaccharide or the Dendrobium officinale oligosaccharide derivative according to the above technical solutions in preparation of anti-aging or immunomodulatory products.
- the products include medicines, foods, formulations and cosmetics.
- a type of the cosmetics includes a face cream, an emulsion, a toning lotion or a repair cream.
- the present disclosure provides a method for extracting the Dendrobium officinale oligosaccharide described in above technical solutions, comprising:
- a temperature for the drying is 50-60°C; a moisture mass content of the stem of Dendrobium officinale after the drying is less than 6%; a mesh number of the sieving is 20-40 meshes;
- step 4 the addition of ethanol to the concentrated water extract of Dendrobium officinale and the precipitation are specifically conducted as follows: adding ethanol with a volume concentration of 95% to the concentrated water extract of Dendrobium officinale until an alcohol concentration of a mixture is 70%-80% in volume percentage, and then precipitating overnight;
- the present disclosure provides a method for preparing the Dendrobium officinale oligosaccharide derivative described in the above technical solutions, comprising:
- a reaction process of the reduction of a fatty acid into a fatty alcohol is as follows: mixing 9-11 mmol of the fatty acid, 18-22 mmol of NaBH 4 , 38-42 mmol of AlCl 3 , 25-29 ml of THF, and 2-4 ml of MeOH for a reaction, and the reaction is conducted under a temperature of 95-105°C for a time of 7.5-8.5 h with a yield of 88-92%;
- a reaction process of the glycosylation is as follows: mixing the alcohol and the saccharide in a molar ratio of 1 : (8-10), and then using cetyl ammonium bromide as a catalyst for catalyzation, and the reaction is conducted under a temperature of 110-115°C for a time of 2.5-3.5 h with a yield of 78-82%.
- the present disclosure provides an anti-aging or immunomodulatory product, where the anti-aging or immunomodulatory product is a face cream, an emulsion, a toning lotion or a repair cream;
- the Dendrobium officinale oligosaccharide Compared with the prior art, the Dendrobium officinale oligosaccharide, the Dendrobium officinale oligosaccharide derivative and the preparation method and use thereof in the present disclosure have at least the following beneficial effects:
- the present disclosure illustrates for the first time the Dendrobium officinale oligosaccharides with a purity of more than or equal to 99% prepared from Dendrobium officinale, and carries out structural analysis to identify the structure of Dendrobium officinale oligosaccharides.
- Dendrobium officinale oligosaccharides can well inhibit collagenase and the like and thus have a strong anti-aging effect. Moreover, they also have a certain activity on TNF- ⁇ and IL-6, and a good immunomodulatory effect.
- the preparation method and active application of Dendrobium officinale oligosaccharides involved in the present disclosure provide a scientific basis for the application of Dendrobium officinale in related directions.
- the Dendrobium officinale oligosaccharide prepared by the present disclosure can be used as an intermediate for the development of Dendrobium officinale series products (such as application in the fields of medicine, food, daily necessities, etc.).
- skin care product in the present disclosure may refer to a skin care toner, a skin care lotion, a skin care mask, a skin cream, etc.; the skin care products in the embodiments of the present disclosure can also refer to cosmetics.
- the present disclosure provides a Dendrobium officinale oligosaccharide, comprising 3-9 glycoside residues and a glucose residue at a non-reducing end; a Dendrobium officinale oligosaccharide containing 6 glycoside residues has a structure represented by formula (I):
- the glycoside residue includes a galactose residue, a mannose residue and a glucose residue; a molar ratio of the galactose residue, the mannose residue and the glucose residue is (3-2) : (2-1) : (2-1), preferably 2: 1: 1.
- the present disclosure provides a method for extracting the Dendrobium officinale oligosaccharide described in above technical solutions, comprising:
- the present disclosure provides use of a Dendrobium officinale oligosaccharide described in above technical solutions in the preparation of anti-aging or immunomodulatory products.
- the products include medicines, foods, formulations and cosmetics.
- the cosmetics include a face cream, an emulsion, a toning lotion or a repair cream.
- the present disclosure provides a Dendrobium officinale oligosaccharide derivative, where the Dendrobium officinale oligosaccharide derivative is generated by reacting the glucose residue of the Dendrobium officinale oligosaccharide according to the above technical solutions with a hydrophobic residue, and the hydrophobic residue includes any one of linear or branched C 1 -C 18 alkyl, C 1 -C 18 alkyl carboxylic acid, C 1 -C 18 alkyl amine, C 1 -C 18 aryl alkyl and C 1 -C 18 alkyl amide, or the hydrophobic residue includes any one of benzoyl, phenylacetyl, and phenylpropionyl (Replacing hydroxy and methoxy with phenyl).
- the present disclosure provides a method for extracting the Dendrobium officinale oligosaccharide derivative described in the above technical solutions, comprising:
- the present disclosure provides use of a Dendrobium officinale oligosaccharide derivative described in above technical solutions in the preparation of anti-aging or immunomodulatory products.
- the products include medicines, foods, formulations and cosmetics; in some embodiments, the cosmetics include a face cream, an emulsion, a toning lotion or a repair cream.
- the present disclosure provides a method for separating and purifying oligosaccharides from Dendrobium officinale.
- the polysaccharide of Dendrobium officinale has a large molecular weight (more than or equal to 100,000) and is difficult to be absorbed through skin cells, and thus mainly acts on the outside of the skin and has a moisturizing effect, while the oligosaccharide formed by enzymatic hydrolysis of polysaccharides has a small molecular weight and is easily absorbed through skin cells, which plays an anti-aging effect. According to the different molecular weights of the two, they can be used differently.
- Dendrobium officinale oligosaccharides can increase the survival rate and survival time of Hacat and RAW264.7 cells. Considering that Dendrobium officinale oligosaccharides may have good anti-aging activities and immunomodulatory activities, the activities on several main target proteins (elastase, collagenase, hyaluronic acid) contributing to aging have been verified. The results show that Dendrobium officinale oligosaccharides have a strong inhibitory effect on collagenase and can effectively alleviate the degradation and metabolism of collagen, thus maintaining the youth state of skin.
- main target proteins elastase, collagenase, hyaluronic acid
- Dendrobium officinale oligosaccharides also have a certain activity on TNF- ⁇ and IL-6, and have a good immunomodulatory effect.
- the present disclosure provides an anti-aging or immunomodulatory product, and the anti-aging or immunomodulatory product is a face cream or an emulsion.
- the anti-aging or immunomodulatory product when the anti-aging or immunomodulatory product is a face cream, it includes components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 7.5-8.5% of stearic acid, 1.5-2.5% of C 16 alcohol, 1.5-2.5% of self-emulsifying monoglyceride, 1.5-2.5% of hydrogenated lanolin, 11-13% of liquid paraffin, 6-8% of glycerin, 1-2% of an emulsifier, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water.
- the anti-aging or immunomodulatory product when the anti-aging or immunomodulatory product is an emulsion, it includes components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 1.3-1.5% of stearic acid, 0.08-0.12% of cetyl alcohol, 1.7-1.9% of 2-ethyl alcohol cetyl stearate, 0.1-0.3% of isopropyl myristate, 0.9-1.1% of 2-hexyl-1-decanol, 7-8% of liquid paraffin, 2.5-3.5% of glycerol, 7-9% of propylene glycol, 0.08-0.12% of triethanolamine, 0.3-0.4% of a carboxyvinyl polymer, 1.5-2.5% of Arlacel 165, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water.
- the present disclosure provides an anti-aging or immunomodulatory product, and the anti-aging or immunomodulatory product is toner.
- the toning lotion includes components in mass percentage: 1-10% of Dendrobium officinale stock solution rich in oligosaccharides, 0.3-0.4% of sodium polyacrylate, 3.5-4.5% of glycerol, 2-3% of 1,3-butanediol, 0.4-0.6% of vitamin B 5 , 0.4-0.6% of arbutin, 0.04-0.06% of EDTA-Na 2 , and the balance of deionized water.
- a method for preparing the toning lotion is as follows: dissolving sodium polyacrylate in water and stirring for fully swelling, and then adding the remaining components and continuing stirring; subsequently, adding the Dendrobium officinale stock solution rich in oligosaccharides and stirring, and then adding deionized water to a constant volume to obtain the toning lotion.
- the present disclosure provides an anti-aging or immunomodulatory product, and the anti-aging or immunomodulatory product is a repair cream; in the present disclosure, the repair cream includes components in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and the balance of deionized water.
- the repair cream includes components in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and
- a method for preparing the repair cream is as follows: adding carbomer into an appropriate amount of deionized water, stirring uniformly, and standing overnight for fully swelling; then adding glycerin, and adjusting the pH value with triethanolamine to increase viscosity of the gel matrix to obtain a carbomer gel;
- the fresh stem of Dendrobium officinale was cut and placed in a blast drying box to dry at 55°C, and the moisture content was measured. When the moisture content reached 6% or less, the stem was smashed and passed through a 20-40 mesh sieve; 50 g of a Dendrobium officinale powder was taken, 2500 mL of ultrapure water was added thereto, then the mixture was subjected to boiling water bath for 2 times with 2 h each time, and the water extracts were merged.
- the purity of the Dendrobium officinale oligosaccharides was identified by high performance liquid chromatography, and the results are shown in FIG. 1 .
- the structure of Dendrobium officinale oligosaccharides was identified by hydrogen nuclear magnetic resonance analysis and C13 nuclear magnetic resonance analysis, and the results are shown in FIG. 2 .
- the drug to be tested was mixed with DPPH (a final concentration of 100 M) and reacted at 30°C for 1 h. 3 repeating wells were set, and a blank control well without drug and a Trolox positive control well were set at the same time.
- the OD value was measured by a microplate reader with a detection wavelength of 515 nm, and the anti-oxidation rate was calculated.
- Anti ⁇ oxidation rate % 1 ⁇ experimental well OD 515 nm / blank well OD 515 nm ⁇ 100 % .
- Table 1 Sample Final reaction concentration Anti-oxidation rate (%) Trolox 25 95.668% Dendrobium officinale oligosaccharide 4% 11.335% Dendrobium officinale oligosaccharide 8% 14.346% Dendrobium officinale oligosaccharide 11% 16.213% Dendrobium officinale oligosaccharide 15% 21.155% Dendrobium officinale oligosaccharide 20% 25.217%
- FIG. 3 is made for a clearer comparison.
- the scavenging ability of DPPH free radicals of Dendrobium officinale oligosaccharides is evaluated in the experiment.
- the results show that the Dendrobium officinale oligosaccharides have a certain anti-oxidation rate (> 20%) at a concentration of 15%-20%.
- FIG. 4 is made for a clearer comparison.
- the elastase inhibition rate of Dendrobium officinale oligosaccharides is evaluated in the experiment.
- the results show that the Dendrobium officinale oligosaccharides have a certain elastase inhibition activity (> 10%) at a concentration of 20%.
- protease protease substrate
- inhibitor 1,10-Phenanthroline
- the collagenase reaction mixture is shown in Table 3.
- Table 3 Composition Content (%) Collagenase buffer solution 60 Collagenase substrate 40
- compositions were designed as follows:
- Collagenase inhibition rate % OD background well ⁇ OD sample well / OD background well ⁇ OD positive control well .
- FIG. 5 is made for a clearer comparison.
- the collagenase inhibition rate of Dendrobium officinale oligosaccharides is evaluated in the experiment.
- the results show that the Dendrobium officinale oligosaccharides have a strong collagenase inhibition activity (> 50%) at a concentration of 0.4%-4%.
- Human immortalized cortical cells (Hacat cells), human hyaluronic acid Elisa kit, distilled water.
- a 96-well plate was inoculated with 100 mL of cell suspension per well, and a concentration of the suspension was 4 ⁇ 10 5 cells/mL. After 24 h of incubation, the original culture medium was discarded, then the cells were washed with PBS for 1-2 times and the serum-free medium containing different concentrations of the drug to be tested was added thereto, and continued to incubate for 24 h. A blank control without drugs and a TGF- ⁇ positive control were set. Then the cells were lysed with ripa lysis buffer solution containing 1% PMSF, the supernatant after centrifugation was taken, and the secretion of hyaluronic acid was detected according to the method provided in the collagen ELISA kit. The OD value was measured by a microplate reader with a detection wavelength of 450 nm. The OD value was substituted into the regression equation of the standard curve to calculate the increase rate of the secretion of hyaluronic acid.
- Table 6 Sample Final reaction concentration Secretion of hyaluronic acid (ng/mL) Blank control 0.2508 Dendrobium officinale oligosaccharide 4% 0.2294 Dendrobium officinale oligosaccharide 8% 0.5530 Dendrobium officinale oligosaccharide 11% 0.3691 Dendrobium officinale oligosaccharide 15% 0.4930 Dendrobium officinale oligosaccharide 20% 0.5392
- FIG. 6 is made for a clearer comparison.
- the secretion-promoting ability of hyaluronic acid of Dendrobium officinale oligosaccharides is evaluated.
- the results show that the Dendrobium officinale oligosaccharides have a certain activity to promote the secretion of hyaluronic acid (> 0.3 ng/mL) at a concentration of 8%-20%.
- RAW264.7 cells TNF- ⁇ kit, IL-6 kit, distilled water.
- the logarithmic-growth RAW264.7 cells were taken and inoculated into 12-well plates after cell counting. The plate was placed in an incubator overnight, and then the cell supernatant was discarded. Different concentrations of Dendrobium officinale oligosaccharides, lipopolysaccharides and basal medium 1640 were added under aseptic operation, and the supernatant after 24 h of intervention was collected and stored at -20°C for later use. The changes in TNF- ⁇ and IL-6 secretion were detected according to the instructions of the ELISA kit. The OD value was measured by a microplate reader with a detection wavelength of 450 nm. The OD value was substituted into the regression equation of the standard curve to calculate the increase rate of TNF- ⁇ and IL-6 secretion.
- Table 7 Sample Final reaction concentration ( ⁇ g/mL) TNF- ⁇ pg/mL Final reaction concentration ( ⁇ g/mL) IL-6 pg/mL Blank control 64.71 1013.72 LPS 1085.13 1406.19 Dendrobium officinale 12.5 53.86 200 1117.33 oligosaccharide Dendrobium officinale oligosaccharide 6.25 35.66 100 1376.42 Dendrobium officinale oligosaccharide 3.125 1062.29 50 1593.01
- FIG. 7 is made for a clearer comparison.
- the effects of Dendrobium officinale oligosaccharide on the immunomodulatory activity of RAW264.7 cells is evaluated.
- the results show that the secretion of TNF- ⁇ by RAW264.7 macrophages is significantly increased at a concentration of 3.125 ⁇ g/mL, which is equivalent to the positive control LPS.
- the secretion of IL-6 by RAW264.7 macrophages can be significantly increased at a concentration of 50 ⁇ g/mL, which is equivalent to the positive control LPS.
- Dendrobium officinale oligosaccharides fatty acids, NaBH 4 , MeOH, metal salts, AlCl 3 , THF, catalysts, etc.
- This example provides an anti-aging or immunomodulatory face cream, comprising components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 7.5-8.5% of stearic acid, 1.5-2.5% of C 16 alcohol, 1.5-2.5% of self-emulsifying monoglyceride, 1.5-2.5% of hydrogenated lanolin, 11-13% of liquid paraffin, 6-8% of glycerin, 1-2% of an emulsifier, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water.
- the face cream of the above formula was prepared according to a conventional method for preparing cosmetics.
- This example provides an anti-aging or immunomodulatory emulsion, comprising components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 1.3-1.5% of stearic acid, 0.08-0.12% of cetyl alcohol, 1.7-1.9% of 2-ethyl alcohol cetyl stearate, 0.1-0.3% of isopropyl myristate, 0.9-1.1% of 2-hexyl-1-decanol, 7-8% of liquid paraffin, 2.5-3.5% of glycerol, 7-9% of propylene glycol, 0.08-0.12% of triethanolamine, 0.3-0.4% of a carboxyvinyl polymer, 1.5-2.5% of Arlacel 165, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water;
- the emulsion of the above formula was prepared according to a conventional method for preparing cosmetics.
- This example provides an anti-aging or immunomodulatory toner, comprising components in mass percentage: 1-10% of Dendrobium officinale stock solution rich in oligosaccharides, 0.3-0.4% of sodium polyacrylate, 3.5-4.5% of glycerol, 2-3% of 1,3-butanediol, 0.4-0.6% of vitamin B 5 , 0.4-0.6% of arbutin, 0.04-0.06% of EDTA-Na 2 , and the balance of deionized water; the method for preparing the toning lotion is as follows: the sodium polyacrylate was dissolved in water, stirred to fully swelling, then the remaining ingredients were added, and continued to stirring; then the Dendrobium officinale stock solution rich in oligosaccharides was added thereto, the mixture was stirred, and then deionized water was added to a constant volume to obtain the toner.
- a preferred solution is as follows: 0.35 g of sodium polyacrylate was dissolved in 70 mL of water, stirred to fully swelling, then the remaining ingredients were added, and continued to stirring; then 10% of the Dendrobium officinale stock solution rich in oligosaccharides obtained in Example 1 was added thereto, the mixture was stirred uniformly, and then deionized water was added to 100 mL and packed.
- This example provides an anti-aging or immunomodulatory repair cream, comprising components in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and the balance of deionized water.
- the method for preparing the repair cream is as follows: the carbomer was taken in an appropriate amount of deionized water, the mixture was stirred uniformly, let stand overnight to fully swelling, then glycerin was added, and the pH value was adjusted with triethanolamine to increase the viscosity of the gel matrix to obtain a carbomer gel; the Dendrobium officinale stock solution rich in oligosaccharides, propylene glycol and deionized water were mixed evenly, then the carbomer gel, essential oil and ethyl p-hydrobenzoate were added thereto, the resulting mixture was stirred until uniform and delicate, distilled water was added to a sufficient amount, and the mixture was grinded evenly to obtain a repair cream.
- a preferred solution is as follows: 6 g of glycerin, 1.5 g of carbomer, 1.5 g of triethanolamine, 6 g of propylene glycol, 0.2 g of ethyl p-hydrobenzoate, 10% of Dendrobium officinale stock solution rich in oligosaccharide obtained in Example 1, and an appropriate amount of deionized water were added to a total weight of 100 g.
- the preparation method is as follows: the carbomer was taken in an appropriate amount of deionized water, the mixture was stirred uniformly, let stand overnight to fully swelling, then glycerin was added, and the pH value was adjusted with triethanolamine to increase the viscosity of the gel matrix to obtain a carbomer gel; a prescription amount of tanshinone extract, propylene glycol and deionized water were mixed evenly, then the carbomer gel, 0.5% of an essential oil and ethyl p-hydrobenzoate were added thereto, the resulting mixture was stirred until uniform and delicate, distilled water was added to a sufficient amount, and the mixture was grinded evenly to obtain a repair cream.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Mycology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Sustainable Development (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Toxicology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Alternative & Traditional Medicine (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
- This patent application claims the benefit and priority of
Chinese Patent Application No. 202110247117.Xfiled on March 05, 2021 - The present disclosure relates to the technical field of natural medicine chemistry, and in particular to a Dendrobium officinale oligosaccharide, a Dendrobium officinale oligosaccharide derivative and a preparation method and use thereof.
- Dendrobium officinale (Dendrobium officinale Kimura et Migo) is a perennial herb of the genus Dendrobium in the family Orchidaceae, which is listed in each edition of the Pharmacopoeia. According to the records in the Pharmacopoeia, it has the effects of such as engendering liquid and nourishing stomach, nourishing yin and clearing heat, moistening lung and boosting kidney, and brightening eyes and strengthening lumbus. Modern pharmacological research shows that Dendrobium officinale has antioxidative, hypoglycemic, immunomodulatory and anti-inflammatory activities. It is recorded in ancient literatures that the stem of Dendrobium officinale can be used for moisturizing skin and treating diabetes. Studies have shown that Dendrobium officinale mainly contains polysaccharides, stilbene, flavonoids, phenanthrene, lignin and other chemical components.
- Aging is an inevitable result of human growth, and the way to delay aging has always been the ultimate proposition in the fields of skin care products and biomedicine. Aging is roughly divided into two categories: physiological aging and pathological aging. Physiological aging refers to the physiological degeneration process that occurs after the mature period, and pathological aging is the senility changes caused by various external factors (including various diseases). The two are actually difficult to distinguish. It is recorded in ancient literatures that Dendrobium officinale has the anti-aging effects, and the natural, green, safe and efficient anti-aging substances in Dendrobium officinale are thus the focus of research.
- At present, many domestic and foreign researchers have conducted research on the extraction and separation of chemical components in various parts of Dendrobium officinale. Most of the researchers mainly obtain small-molecule phenol components or polysaccharides with a molecular weight of more than 100,000. Some researchers have isolated 20 compounds from Dendrobium officinale, mainly bibenzil components, and have found that the small-molecule phenol components of Dendrobium officinale have antioxidative, anti-inflammatory and anti-tumor effects through activity screening. Some researchers have extracted and separated two polysaccharides from Dendrobium officinale with a molecular weight of 7.4×105 Da and 5.4×105 Da, respectively. Some researchers have used a method of water extraction, alcohol precipitation and sulfuric acid hydrolysis to obtain polysaccharides from Dendrobium officinale, and have found that the polysaccharides of Dendrobium officinale influence the count of peripheral white blood cells in mice through activity screening, indicating an immunomodulatory effect. Some researchers have obtained polysaccharides from Dendrobium officinale by ultrasonic extraction and have found that the polysaccharides of Dendrobium officinale influence the SOD, MDA and CAT of Drosophila through activity screening, indicating an antioxidative activity. Some researchers have demonstrated that there are mainly four homogeneous polysaccharides among polysaccharides of Dendrobium officinale, with a molecular weight in a range of 6,800-1.78×105 Da. The previous research work mostly concentrates on the study of the pharmacological activity of the small-molecule phenol components and the polysaccharides, whereas there are few reports on the research of oligosaccharides.
- In view of this, the present disclosure provides a Dendrobium officinale oligosaccharide, a Dendrobium officinale oligosaccharide derivative and a preparation method and use thereof. It is illustrated that the Dendrobium officinale oligosaccharide has anti-aging and immunomodulatory effects, and is suitable for applying to skin cosmetics, health foods and medicines with anti-aging and immunomodulatory effects.
- In order to achieve the above objectives, the present disclosure mainly provides the following technical solutions:
- The present disclosure provides a Dendrobium officinale oligosaccharide, comprising 3-9 glycoside residues and a glucose residue at a non-reducing end.
- In some embodiments, the Dendrobium officinale oligosaccharide comprises 6 glycoside residues.
-
- In some embodiments, the glycoside residue includes a galactose residue, a mannose residue and a glucose residue.
- In some embodiments, a molar ratio of the galactose residue, the mannose residue and the glucose residue is (3-2) : (2-1) : (2-1).
- In some embodiments, a molar ratio of the galactose residue, the mannose residue and the glucose residue is 2 : 1 : 1.
- The present disclosure provides a Dendrobium officinale oligosaccharide derivative, where the Dendrobium officinale oligosaccharide derivative is generated by reacting the glucose residue of the Dendrobium officinale oligosaccharide according to the above technical solutions with a hydrophobic residue, and the hydrophobic residue includes any one of linear or branched C1-C18 alkyl, C1-C18 alkyl carboxylic acid, C1-C18 alkyl amine, C1-C18 aryl alkyl and C1-C18 alkyl amide, or
the hydrophobic residue includes any one of benzoyl, phenylacetyl and phenylpropionyl. - The present disclosure provides use of the Dendrobium officinale oligosaccharide or the Dendrobium officinale oligosaccharide derivative according to the above technical solutions in preparation of anti-aging or immunomodulatory products.
- In some embodiments, the products include medicines, foods, formulations and cosmetics.
- In some embodiments, a type of the cosmetics includes a face cream, an emulsion, a toning lotion or a repair cream.
- The present disclosure provides a method for extracting the Dendrobium officinale oligosaccharide described in above technical solutions, comprising:
- 1) preparation of a Dendrobium officinale powder: drying a stem of Dendrobium officinale, then smashing and sieving to obtain a Dendrobium officinale powder;
- 2) preparation of a water extract of Dendrobium officinale: mixing the Dendrobium officinale powder with water, then subjecting to a boiling water bath for one or more times, and then merging water extracts to obtain a water extract of Dendrobium officinale;
- 3) preparation of a concentrated water extract of Dendrobium officinale: centrifuging the water extract of Dendrobium officinale, and then concentrating under reduced pressure to obtain a concentrated water extract of Dendrobium officinale;
- 4) preparation of a redissolving liquid: adding ethanol to the concentrated water extract of Dendrobium officinale, precipitating, centrifuging and then discarding a supernatant to obtain a precipitate; adding water to the obtained precipitate for redissolving to obtain a redissolving liquid;
- 5) preparation of an aqueous solution of Dendrobium officinale oligosaccharide: deproteinizing the redissolving liquid, and freeze-drying to obtain a crude polysaccharide of Dendrobium officinale; adding water to dissolve the crude polysaccharide of Dendrobium officinale, then adding cellulase for a reaction, followed by inactivating and centrifuging, and discarding a precipitate to obtain an aqueous solution of Dendrobium officinale oligosaccharide;
- 6) preparation of the Dendrobium officinale oligosaccharide: purifying the aqueous solution of Dendrobium officinale oligosaccharide to obtain the Dendrobium officinale oligosaccharide.
- In some embodiments, in step 1), a temperature for the drying is 50-60°C; a moisture mass content of the stem of Dendrobium officinale after the drying is less than 6%; a mesh number of the sieving is 20-40 meshes;
- in step 2), the Dendrobium officinale powder and water are mixed in a mass-volume ratio of 1 : (50-80) g/mL; the boiling water bath is performed for 2-3 times; a time for each boiling water bath is 1-2 h;
- in step 3), the centrifugation is conducted under conditions of 3000-4000 rpm/min, 8-12 min and room temperature; the concentration under reduced pressure is conducted under conditions of a rotary evaporation method, an ethanol recycling temperature of less than 50°C, and a pressure of 0.7 Pa-0.9 Pa; a material-liquid mass-volume ratio of the concentrated water extract of Dendrobium officinale is 1 : (5-10) g/mL.
- In some embodiments, in step 4), the addition of ethanol to the concentrated water extract of Dendrobium officinale and the precipitation are specifically conducted as follows: adding ethanol with a volume concentration of 95% to the concentrated water extract of Dendrobium officinale until an alcohol concentration of a mixture is 70%-80% in volume percentage, and then precipitating overnight;
- the centrifugation is conducted under conditions of 3500-4500 rpm, 18-22 min and room temperature; a weight-volume ratio of the precipitate and water for redissolving is 1 : (4-6) g/mL;
- in step 5), the deproteinization of the redissolving liquid is conducted by a Sevage method;
- a temperature for the freeze-drying is 45°C;
- the addition of water to dissolve the crude polysaccharide of Dendrobium officinale is conducted as follows: adding water to the crude polysaccharide of Dendrobium officinale for dissolving until 4.5-5.5 mg/mL;
- an added amount of the cellulase is 2%-4% of a weight of the crude polysaccharide of Dendrobium officinale;
- after adding the cellulase, the reaction is conducted under a reaction temperature of 55-65°C for a reaction time of 2 h-4 h;
- the inactivation is conducted by boiling for 25-35 min;
- the centrifugation is conducted under conditions of 3500-4500 rpm, 15-25 min and room temperature;
- an oligosaccharide content in the aqueous solution of Dendrobium officinale oligosaccharide is greater than 80%;
- in step 6), the purification is conducted by passing through a G75 gel column; a purity of the Dendrobium officinale oligosaccharide is 99.86%.
- The present disclosure provides a method for preparing the Dendrobium officinale oligosaccharide derivative described in the above technical solutions, comprising:
- 1) reducing a fatty acid into a fatty alcohol;
- 2) glycosylating the fatty alcohol with the Dendrobium officinale oligosaccharide to obtain the Dendrobium officinale oligosaccharide derivative.
- In some embodiments, in step 1), a reaction process of the reduction of a fatty acid into a fatty alcohol is as follows: mixing 9-11 mmol of the fatty acid, 18-22 mmol of NaBH4, 38-42 mmol of AlCl3, 25-29 ml of THF, and 2-4 ml of MeOH for a reaction, and the reaction is conducted under a temperature of 95-105°C for a time of 7.5-8.5 h with a yield of 88-92%;
in step 2), a reaction process of the glycosylation is as follows: mixing the alcohol and the saccharide in a molar ratio of 1 : (8-10), and then using cetyl ammonium bromide as a catalyst for catalyzation, and the reaction is conducted under a temperature of 110-115°C for a time of 2.5-3.5 h with a yield of 78-82%. - The present disclosure provides an anti-aging or immunomodulatory product, where the anti-aging or immunomodulatory product is a face cream, an emulsion, a toning lotion or a repair cream;
- the face cream includes in mass percentage: 0.4-0.6% of a Dendrobium officinale stock solution rich in oligosaccharides, 7.5-8.5% of stearic acid, 1.5-2.5% of C16 alcohol, 1.5-2.5% of self-emulsifying monoglyceride, 1.5-2.5% of hydrogenated lanolin, 11-13% of liquid paraffin, 6-8% of glycerin, 1-2% of an emulsifier, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water;
- the emulsion includes in mass percentage: 0.4-0.6% of a Dendrobium officinale stock solution rich in oligosaccharides, 1.3-1.5% of stearic acid, 0.08-0.12% of cetyl alcohol, 1.7-1.9% of 2-ethyl alcohol cetyl stearate, 0.1-0.3% of isopropyl myristate, 0.9-1.1% of 2-hexyl-1-decanol, 7-8% of liquid paraffin, 2.5-3.5% of glycerol, 7-9% of propylene glycol, 0.08-0.12% of triethanolamine, 0.3-0.4% of a carboxyvinyl polymer, 1.5-2.5% of Arlacel 165, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water;
- the toning lotion includes in mass percentage: 1-10% of a Dendrobium officinale stock solution rich in oligosaccharides, 0.3-0.4% of sodium polyacrylate, 3.5-4.5% of glycerol, 2-3% of 1,3-butanediol, 0.4-0.6% of vitamin B5, 0.4-0.6% of arbutin, 0.04-0.06% of EDTA-Na2, and the balance of deionized water;
- the repair cream includes in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of a Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and the balance of deionized water.
- Compared with the prior art, the Dendrobium officinale oligosaccharide, the Dendrobium officinale oligosaccharide derivative and the preparation method and use thereof in the present disclosure have at least the following beneficial effects:
- In one aspect, the present disclosure illustrates for the first time the Dendrobium officinale oligosaccharides with a purity of more than or equal to 99% prepared from Dendrobium officinale, and carries out structural analysis to identify the structure of Dendrobium officinale oligosaccharides.
- Further, the present disclosure conducts for the first time a systematic study on the anti-aging activity of Dendrobium officinale oligosaccharides, and has found that Dendrobium officinale oligosaccharides can well inhibit collagenase and the like and thus have a strong anti-aging effect. Moreover, they also have a certain activity on TNF-α and IL-6, and a good immunomodulatory effect.
- In another aspect, the preparation method and active application of Dendrobium officinale oligosaccharides involved in the present disclosure provide a scientific basis for the application of Dendrobium officinale in related directions.
- In yet another aspect, the Dendrobium officinale oligosaccharide prepared by the present disclosure can be used as an intermediate for the development of Dendrobium officinale series products (such as application in the fields of medicine, food, daily necessities, etc.).
-
-
FIGs. 1-3 show the structure and purity identification HPLC-ELSD, NMR and MS spectra of Dendrobium officinale oligosaccharides of the present disclosure: -
FIG. 1 shows the purity identification HPLC-ELSD spectrum of Dendrobium officinale oligosaccharides; -
FIG. 2 shows the 1H-NMR and 13C-NMR spectra of Dendrobium officinale oligosaccharides, whereFIG. 2A is a 1H-NMR spectrum, andFIG. 2B is a 13C-NMR spectrum; -
FIGs. 3-6 show the test results of the anti-aging activity of Dendrobium officinale oligosaccharides: -
FIG. 3 shows the anti-oxidation rate of Dendrobium officinale oligosaccharides based on the scavenging rate of DPPH free radicals (oligosaccharide concentrations of 4%, 8%, 11%, 15%, 20%); where the ordinate is the anti-oxidation rate % represented by the scavenging rate of DPPH free radicals, and the abscissa (from 1 to 5) corresponds to the oligosaccharide concentration of 4%, 8%, 11%, 15%, 20%, respectively; -
FIG. 4 shows the inhibition rate of Dendrobium officinale oligosaccharides on elastase activity (oligosaccharide concentrations of 4%, 8%, 11%, 15%, 20%); where the ordinate is the elastase inhibition rate %, and the abscissa (from 1 to 5) corresponds to the oligosaccharide concentration of 4%, 8%, 11%, 15%, 20%, respectively; -
FIG. 5 shows the inhibition rate of Dendrobium officinale oligosaccharides on collagenase activity (oligosaccharide concentrations of 0.4%, 0.8%, 1%, 2%, 4%); where the ordinate is the collagenase inhibition rate %, and the abscissa (from 1 to 5) corresponds to the oligosaccharide concentration of 0.4%, 0.8%, 1%, 2%, 4%, respectively; -
FIG. 6 shows the activity of Dendrobium officinale oligosaccharides on promoting the secretion of hyaluronic acid (oligosaccharide concentrations of 4%, 8%, 11%, 15%, 20%); where the ordinate is the secretion of hyaluronic acid (ng/mL), and the abscissa (from 1 to 5) corresponds to the oligosaccharide concentration of 4%, 8%, 11%, 15%, 20%, respectively; -
FIG. 7 shows the effect of Dendrobium officinale oligosaccharides on the immunomodulatory activity of RAW264.7 cells (oligosaccharide concentrations of 3.125 µg/mL, 6.25 µg/mL, 12.5 µg/mL, 50 µg/mL, 100 µg/mL, 200 µg/mL); where A inFIG. 7 shows the effect of oligosaccharides on TNF-α secretion, the ordinate is TNF-α secretion pg/mL and the abscissa (from 1 to 5) corresponds to blank, lipopolysaccharide LPS and oligosaccharide with a final reaction concentration of 12.5 µg/mL, 6.25 µg/mL, 3.125 µg/mL, respectively; B inFIG. 7 shows the effect of oligosaccharides on IL-6 secretion, the ordinate is IL-6 secretion pg/mL, and the abscissa (from 1 to 5) corresponds to blank, lipopolysaccharide LPS and oligosaccharide with a final reaction concentration of 200 µg/mL, 100 µg/mL, 50 µg/mL, respectively. - In order to further explain the technical means and effects of the present disclosure to achieve the intended purpose of the present disclosure, the specific implementations, structures, features and effects of the disclosure according to the present disclosure will be described in detail below with reference to the accompanying drawings and preferred embodiments. In the following description, different "one embodiment" or "an embodiment" do not necessarily refer to the same embodiment. In addition, specific features, structures or characteristics in one or more embodiments may be combined in any suitable form.
- The term "skin care product" in the present disclosure may refer to a skin care toner, a skin care lotion, a skin care mask, a skin cream, etc.; the skin care products in the embodiments of the present disclosure can also refer to cosmetics.
-
- Herein, the glycoside residue includes a galactose residue, a mannose residue and a glucose residue; a molar ratio of the galactose residue, the mannose residue and the glucose residue is (3-2) : (2-1) : (2-1), preferably 2: 1: 1.
- The present disclosure provides a method for extracting the Dendrobium officinale oligosaccharide described in above technical solutions, comprising:
- 1) preparation of Dendrobium officinale powder: drying a stem of Dendrobium officinale, then smashing and sieving to obtain the Dendrobium officinale powder;
In some embodiments, a temperature for the drying is 50-60°C; a moisture mass content of the stem of Dendrobium officinale after the drying is less than 6%; and a mesh number of the sieving is 20-40 meshes; - 2) preparation of a water extract of Dendrobium officinale: mixing the Dendrobium officinale powder with water, then subjecting to a boiling water bath for one or more times, and merging the water extracts obtained after the boiling water bath to obtain a water extract of Dendrobium officinale;
in some embodiments, the Dendrobium officinale powder and water are mixed according to a mass-volume ratio of 1: (50-80) g/mL; the boiling water bath is performed for 2-3 times; and a time for each boiling water bath is 1-2 h; - 3) preparation of a concentrated water extract of Dendrobium officinale: centrifuging the water extract of Dendrobium officinale, and then concentrating under reduced pressure to obtain a concentrated water extract of Dendrobium officinale;
in some embodiments, the centrifugation is conducted under 3000-4000 rpm/min, 8-12 min, and room temperature; the concentration under reduced pressure is conducted by using a rotary evaporation method, an ethanol recycling temperature of less than 50°C and a pressure of 0.7 Pa-0.9 Pa; a material-liquid mass-volume ratio of the concentrated water extract of Dendrobium officinale is 1 : (5-10) g/mL; - 4) preparation of a redissolving liquid: adding ethanol to the concentrated water extract of Dendrobium officinale, precipitating, centrifuging and then discarding a supernatant to obtain a precipitate; and then adding water to the obtained precipitate for redissolving to obtain a redissolving liquid;
in some embodiments, ethanol with a volume concentration of 95% is added to the concentrated water extract of Dendrobium officinale until an alcohol concentration of the mixture is 70%-80% by volume percentage, and then the overnight precipitation is carried out; the conditions of centrifugation are 3500-4500 rpm, 18-22 min, and room temperature; and water is added according to a weight-volume ratio of the precipitate and water of 1: (4-6) g/mL for redissolving; - 5) preparation of an aqueous solution of Dendrobium officinale oligosaccharide: deproteinizing the redissolving liquid, and freeze-drying to obtain a crude polysaccharide of Dendrobium officinale; and adding water to dissolve the crude polysaccharide of Dendrobium officinale, then adding cellulase for a reaction, followed by inactivating and centrifuging, and discarding a precipitate to obtain an aqueous solution of Dendrobium officinale oligosaccharide;
in some embodiments, the redissolving liquid is deproteinized by a Sevage method; the freeze-drying temperature is 45°C; adding water to dissolve the crude polysaccharide of Dendrobium officinale to 4.5-5.5 mg/mL; an added amount of the cellulase is 2%-4% of the weight of the crude polysaccharide of Dendrobium officinale; after the cellulase is added, the reaction is conducted under a reaction temperature of 55-65°C, and a reaction time of 2 h-4 h; inactivating by boiling for 25-35 min; the centrifugation are conducted under 3500-4500 rpm, 15-25 min, and room temperature; the oligosaccharide content in the aqueous solution of Dendrobium officinale oligosaccharide is greater than 80%; - 6) preparation of Dendrobium officinale oligosaccharide: purifying the aqueous solution of Dendrobium officinale oligosaccharide to obtain the Dendrobium officinale oligosaccharide;
in some embodiments, the purification is conducted by using a G75 gel column; the purity of the Dendrobium officinale oligosaccharide is 99.86%. - The present disclosure provides use of a Dendrobium officinale oligosaccharide described in above technical solutions in the preparation of anti-aging or immunomodulatory products.
- In some embodiments, the products include medicines, foods, formulations and cosmetics. In some embodiments, the cosmetics include a face cream, an emulsion, a toning lotion or a repair cream.
- The present disclosure provides a Dendrobium officinale oligosaccharide derivative, where the Dendrobium officinale oligosaccharide derivative is generated by reacting the glucose residue of the Dendrobium officinale oligosaccharide according to the above technical solutions with a hydrophobic residue, and the hydrophobic residue includes any one of linear or branched C1-C18 alkyl, C1-C18 alkyl carboxylic acid, C1-C18 alkyl amine, C1-C18 aryl alkyl and C1-C18 alkyl amide, or
the hydrophobic residue includes any one of benzoyl, phenylacetyl, and phenylpropionyl (Replacing hydroxy and methoxy with phenyl). - The present disclosure provides a method for extracting the Dendrobium officinale oligosaccharide derivative described in the above technical solutions, comprising:
- 1) reducing a fatty acid into a fatty alcohol;
in some embodiments, a reaction process of reducing the fatty acid into the fatty alcohol is as follows: mixing 10 mmol of fatty acid, 20 mmol of NaBH4, 40 mmol of AlCl3, 27 ml of THF, 3 ml of MeOH for a reaction, the reaction temperature is 100°C, the reaction time is 8 h, and the yield is 90%; - 2) glycosylating the fatty alcohol with Dendrobium officinale oligosaccharide;
in some embodiments, performing the glycosylation reaction of fatty alcohols and Dendrobium officinale oligosaccharides obtained by reduction, the glycosylation reaction is conducted as follows: a molar ratio of alcohol to saccharide is 1: (8-10), the catalyst is cetylammonium bromide, the reaction temperature is 110-115°C, the reaction time is 3 h, and the yield is 80%. - The present disclosure provides use of a Dendrobium officinale oligosaccharide derivative described in above technical solutions in the preparation of anti-aging or immunomodulatory products.
- In some embodiments, the products include medicines, foods, formulations and cosmetics; in some embodiments, the cosmetics include a face cream, an emulsion, a toning lotion or a repair cream.
- The present disclosure provides a method for separating and purifying oligosaccharides from Dendrobium officinale. The polysaccharide of Dendrobium officinale has a large molecular weight (more than or equal to 100,000) and is difficult to be absorbed through skin cells, and thus mainly acts on the outside of the skin and has a moisturizing effect, while the oligosaccharide formed by enzymatic hydrolysis of polysaccharides has a small molecular weight and is easily absorbed through skin cells, which plays an anti-aging effect. According to the different molecular weights of the two, they can be used differently.
- On the other hand, it is also found that Dendrobium officinale oligosaccharides can increase the survival rate and survival time of Hacat and RAW264.7 cells. Considering that Dendrobium officinale oligosaccharides may have good anti-aging activities and immunomodulatory activities, the activities on several main target proteins (elastase, collagenase, hyaluronic acid) contributing to aging have been verified. The results show that Dendrobium officinale oligosaccharides have a strong inhibitory effect on collagenase and can effectively alleviate the degradation and metabolism of collagen, thus maintaining the youth state of skin. They also have a certain inhibitory effect on elastase, and meanwhile a certain activity to promote the secretion of hyaluronic acid. Dendrobium officinale oligosaccharides also have a certain activity on TNF-α and IL-6, and have a good immunomodulatory effect.
- The present disclosure provides an anti-aging or immunomodulatory product, and the anti-aging or immunomodulatory product is a face cream or an emulsion.
- When the anti-aging or immunomodulatory product is a face cream, it includes components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 7.5-8.5% of stearic acid, 1.5-2.5% of C16 alcohol, 1.5-2.5% of self-emulsifying monoglyceride, 1.5-2.5% of hydrogenated lanolin, 11-13% of liquid paraffin, 6-8% of glycerin, 1-2% of an emulsifier, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water.
- When the anti-aging or immunomodulatory product is an emulsion, it includes components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 1.3-1.5% of stearic acid, 0.08-0.12% of cetyl alcohol, 1.7-1.9% of 2-ethyl alcohol cetyl stearate, 0.1-0.3% of isopropyl myristate, 0.9-1.1% of 2-hexyl-1-decanol, 7-8% of liquid paraffin, 2.5-3.5% of glycerol, 7-9% of propylene glycol, 0.08-0.12% of triethanolamine, 0.3-0.4% of a carboxyvinyl polymer, 1.5-2.5% of Arlacel 165, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water.
- The present disclosure provides an anti-aging or immunomodulatory product, and the anti-aging or immunomodulatory product is toner. In the present disclosure, the toning lotion includes components in mass percentage: 1-10% of Dendrobium officinale stock solution rich in oligosaccharides, 0.3-0.4% of sodium polyacrylate, 3.5-4.5% of glycerol, 2-3% of 1,3-butanediol, 0.4-0.6% of vitamin B5, 0.4-0.6% of arbutin, 0.04-0.06% of EDTA-Na2, and the balance of deionized water.
- In the present disclosure, a method for preparing the toning lotion is as follows: dissolving sodium polyacrylate in water and stirring for fully swelling, and then adding the remaining components and continuing stirring; subsequently, adding the Dendrobium officinale stock solution rich in oligosaccharides and stirring, and then adding deionized water to a constant volume to obtain the toning lotion.
- The present disclosure provides an anti-aging or immunomodulatory product, and the anti-aging or immunomodulatory product is a repair cream; in the present disclosure, the repair cream includes components in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and the balance of deionized water.
- In the present disclosure, a method for preparing the repair cream is as follows: adding carbomer into an appropriate amount of deionized water, stirring uniformly, and standing overnight for fully swelling; then adding glycerin, and adjusting the pH value with triethanolamine to increase viscosity of the gel matrix to obtain a carbomer gel;
- mixing the Dendrobium officinale stock solution rich in oligosaccharides, propylene glycol and deionized water, then adding the carbomer gel, essential oil and ethyl p-hydrobenzoate thereto and stirring to an uniform and delicate state; adding distilled water to a sufficient amount, and grinding evenly to obtain the repair cream.
- Hereinafter, the present disclosure is further described in detail with reference to the specific examples as follows.
- In this example, substantially, Dendrobium officinale oligosaccharides were separated and purified from a stem of Dendrobium officinale, and further subjected to structural identification:
- The fresh stem of Dendrobium officinale was cut and placed in a blast drying box to dry at 55°C, and the moisture content was measured. When the moisture content reached 6% or less, the stem was smashed and passed through a 20-40 mesh sieve; 50 g of a Dendrobium officinale powder was taken, 2500 mL of ultrapure water was added thereto, then the mixture was subjected to boiling water bath for 2 times with 2 h each time, and the water extracts were merged. Then a centrifugation was conducted at 3000-4000 rpm for 10 min at room temperature of 25°C to obtain a water extract of Dendrobium officinale; the water extract of Dendrobium officinale was concentrated under reduced pressure to 500 mL to obtain a concentrated water extract of Dendrobium officinale. An appropriate amount of 95% ethanol was added to the concentrated water extract of Dendrobium officinale until an alcohol concentration of the mixture was 70-80%, then the mixture was precipitated overnight, centrifuged at 4000 rpm for 20 min at room temperature of 25°C, and the supernatant was discarded to obtain a precipitate; water was added according to the ratio of the weight of the precipitate to the volume of water of 1 : 5 (m : v) (g/mL) for redissolving to obtain a redissolving liquid. The redissolving liquid was deproteinized by the Sevage method, and then freeze-dried to obtain a crude polysaccharide of Dendrobium officinale. 200 mg of the crude polysaccharide of Dendrobium officinale was taken and dissolved with water to 5 mg/mL, cellulase was added thereto in 2%-4% of the weight of the polysaccharide of Dendrobium officinale and mixed evenly, then the mixture was reacted at 60°C for 2 h-4 h, boiled for 30 min for inactivation, centrifuged at 4000 rpm for 20 min at room temperature of 25°C, and a precipitate was discarded to obtain an aqueous solution of Dendrobium officinale oligosaccharide (the content of oligosaccharides in the aqueous solution of Dendrobium officinale oligosaccharide is greater than 80%). An appropriate amount of the aqueous solution of Dendrobium officinale oligosaccharide was taken and passed through a G75 gel column to obtain 150 mg of purified Dendrobium officinale oligosaccharide (with a purity of 99.86% and a molecular weight of about 1,000).
- The purity of the Dendrobium officinale oligosaccharides was identified by high performance liquid chromatography, and the results are shown in
FIG. 1 . The structure of Dendrobium officinale oligosaccharides was identified by hydrogen nuclear magnetic resonance analysis and C13 nuclear magnetic resonance analysis, and the results are shown inFIG. 2 . - DPPH, water-soluble vitamin E (Trolox) (Trolox dissolved in absolute ethanol, with a concentration of 10 mM, stored at -20°C), pure water.
- The drug to be tested was mixed with DPPH (a final concentration of 100 M) and reacted at 30°C for 1 h. 3 repeating wells were set, and a blank control well without drug and a Trolox positive control well were set at the same time. The OD value was measured by a microplate reader with a detection wavelength of 515 nm, and the anti-oxidation rate was calculated.
- As shown in Table 1.
Table 1 Sample Final reaction concentration Anti-oxidation rate (%) Trolox 25 95.668% Dendrobium officinale oligosaccharide 4% 11.335% Dendrobium officinale oligosaccharide 8% 14.346% Dendrobium officinale oligosaccharide 11% 16.213% Dendrobium officinale oligosaccharide 15% 21.155% Dendrobium officinale oligosaccharide 20% 25.217% - According to the data in Table 1,
FIG. 3 is made for a clearer comparison. As can be seen fromFIG. 3 and Table 1, the scavenging ability of DPPH free radicals of Dendrobium officinale oligosaccharides is evaluated in the experiment. The results show that the Dendrobium officinale oligosaccharides have a certain anti-oxidation rate (> 20%) at a concentration of 15%-20%. - Sample, positive control of catechin, Tris, HCl, porcine pancreatic elastase, N-succinyl-alanine-alanine-alanine-p-nitroaniline, DMSO.
-
- (1) Preparation of solution
- Preparation of a sample solution: 1 mg/mL sample solution was prepared (pure water or a buffer solution was used for preparation, and if insoluble in water or the buffer solution, the sample was firstly dissolved with DMSO, and then water or the buffer solution was added. In principle, the content of DMSO should not exceed 5%).
- Preparation of a positive control: 1 mg/mL catechin;
- Preparation of a buffer solution: 0.1 M of Tris-HCl buffer solution, PH = 8.0;
- Preparation of a reaction substrate solution:
N-succinyl-alanine-alanine-alanine-p-nitroaniline (AAAPVN) solution (2 mM); - Preparation: 28.5 µL of porcine pancreatic elastase solution (0.171 U/mL) was taken and dissolved in 10 mL of Tris-HCl buffer solution.
- (2) The solution of 50 µL of sample, 50 µL of porcine pancreatic elastase and 100 µL of reaction substrate was added to a 96-well plate.
- (3) After keeping at room temperature for 5 min, an absorbance at 420 nm was measured.
- As shown in Table 2.
Table 2 Sample Final reaction concentration Elastase inhibition rate % epicatechin gallate 100 µg/ml 68.540% Dendrobium officinale oligosaccharide 4% -2.135% Dendrobium officinale oligosaccharide 8% 3.886% Dendrobium officinale oligosaccharide 11% 8.417% Dendrobium officinale oligosaccharide 15% 9.723% Dendrobium officinale oligosaccharide 20% 15.827% - According to the data in Table 2,
FIG. 4 is made for a clearer comparison. As can be seen fromFIG. 4 and Table 2, the elastase inhibition rate of Dendrobium officinale oligosaccharides is evaluated in the experiment. The results show that the Dendrobium officinale oligosaccharides have a certain elastase inhibition activity (> 10%) at a concentration of 20%. - Protease buffer solution, protease, protease substrate, inhibitor (1,10-Phenanthroline). All reagents were stored at -20°C.
- The collagenase reaction mixture is shown in Table 3.
Table 3 Composition Content (%) Collagenase buffer solution 60 Collagenase substrate 40 -
- a. Background blank well: 100 µL/well of protease buffer solution.
- b. Sample well: 100 µL, prepared into different concentrations.
- c. Positive control well: 10 µL of protease + 90 µL of protease buffer solution.
- d. Inhibitor control well: 10 µL of protease + 2 µL of inhibitor + 88 µL of protease buffer solution as shown in Table 4.
- (3) After adding reagents according to the above groups, 100 µL of collagenase reaction mixture was added to each well, incubated in the dark, and then the OD value at 345 nm was measured.
-
- As shown in Table 5.
Table 5 Sample Final reaction concentration Collagenase inhibition rate (%) Positive inhibitor 1% 102.23% Dendrobium officinale oligosaccharide 0.4% 50.32% Dendrobium officinale oligosaccharide 0.8% 63.63% Dendrobium officinale oligosaccharide 1% 72.20% Dendrobium officinale oligosaccharide 2% 84.80% Dendrobium officinale oligosaccharide 4% 110.54% - According to the data in Table 5,
FIG. 5 is made for a clearer comparison. As can be seen fromFIG. 5 and Table 5, the collagenase inhibition rate of Dendrobium officinale oligosaccharides is evaluated in the experiment. The results show that the Dendrobium officinale oligosaccharides have a strong collagenase inhibition activity (> 50%) at a concentration of 0.4%-4%. - Human immortalized cortical cells (Hacat cells), human hyaluronic acid Elisa kit, distilled water.
- A 96-well plate was inoculated with 100 mL of cell suspension per well, and a concentration of the suspension was 4×105 cells/mL. After 24 h of incubation, the original culture medium was discarded, then the cells were washed with PBS for 1-2 times and the serum-free medium containing different concentrations of the drug to be tested was added thereto, and continued to incubate for 24 h. A blank control without drugs and a TGF-β positive control were set. Then the cells were lysed with ripa lysis buffer solution containing 1% PMSF, the supernatant after centrifugation was taken, and the secretion of hyaluronic acid was detected according to the method provided in the collagen ELISA kit. The OD value was measured by a microplate reader with a detection wavelength of 450 nm. The OD value was substituted into the regression equation of the standard curve to calculate the increase rate of the secretion of hyaluronic acid.
- As shown in Table 6.
Table 6 Sample Final reaction concentration Secretion of hyaluronic acid (ng/mL) Blank control 0.2508 Dendrobium officinale oligosaccharide 4% 0.2294 Dendrobium officinale oligosaccharide 8% 0.5530 Dendrobium officinale oligosaccharide 11% 0.3691 Dendrobium officinale oligosaccharide 15% 0.4930 Dendrobium officinale oligosaccharide 20% 0.5392 - According to the data in Table 6,
FIG. 6 is made for a clearer comparison. As can be seen fromFIG. 6 and Table 6, the secretion-promoting ability of hyaluronic acid of Dendrobium officinale oligosaccharides is evaluated. The results show that the Dendrobium officinale oligosaccharides have a certain activity to promote the secretion of hyaluronic acid (> 0.3 ng/mL) at a concentration of 8%-20%. - RAW264.7 cells, TNF-α kit, IL-6 kit, distilled water.
- The logarithmic-growth RAW264.7 cells were taken and inoculated into 12-well plates after cell counting. The plate was placed in an incubator overnight, and then the cell supernatant was discarded. Different concentrations of Dendrobium officinale oligosaccharides, lipopolysaccharides and basal medium 1640 were added under aseptic operation, and the supernatant after 24 h of intervention was collected and stored at -20°C for later use. The changes in TNF-α and IL-6 secretion were detected according to the instructions of the ELISA kit. The OD value was measured by a microplate reader with a detection wavelength of 450 nm. The OD value was substituted into the regression equation of the standard curve to calculate the increase rate of TNF-α and IL-6 secretion.
- As shown in Table 7.
Table 7 Sample Final reaction concentration (µg/mL) TNF-α pg/mL Final reaction concentration (µg/mL) IL-6 pg/mL Blank control 64.71 1013.72 LPS 1085.13 1406.19 Dendrobium officinale 12.5 53.86 200 1117.33 oligosaccharide Dendrobium officinale oligosaccharide 6.25 35.66 100 1376.42 Dendrobium officinale oligosaccharide 3.125 1062.29 50 1593.01 - According to the data in Table 7,
FIG. 7 is made for a clearer comparison. As can be seen fromFIG. 7 and Table 7, the effects of Dendrobium officinale oligosaccharide on the immunomodulatory activity of RAW264.7 cells is evaluated. The results show that the secretion of TNF-α by RAW264.7 macrophages is significantly increased at a concentration of 3.125 µg/mL, which is equivalent to the positive control LPS. The secretion of IL-6 by RAW264.7 macrophages can be significantly increased at a concentration of 50 µg/mL, which is equivalent to the positive control LPS. -
- 1) Reducing a C6 fatty acid into a fatty alcohol: 10 mmol of fatty acid, 20 mmol of NaBH4, 40 mmol of AlCl3, 27 mL of THF and 3 mL of MeOH were reacted at a temperature of 100°C for a time of 8 h with a yield of 90%;
- 2) Glycosylation: the reduced fatty alcohol and the Dendrobium officinale oligosaccharide were subjected to a glycosylation reaction with a molar ratio of the alcohol and the saccharide of 1 : (8-10); the catalyst was cetyl ammonium bromide; the reaction was conducted under a temperature of 110-115°C for a time of 3 h with a yield of 80%.
- The reaction results show that Dendrobium officinale oligosaccharides with terminal glycosides can also undergo the glycosylation reaction with fatty acids.
- This example provides an anti-aging or immunomodulatory face cream, comprising components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 7.5-8.5% of stearic acid, 1.5-2.5% of C16 alcohol, 1.5-2.5% of self-emulsifying monoglyceride, 1.5-2.5% of hydrogenated lanolin, 11-13% of liquid paraffin, 6-8% of glycerin, 1-2% of an emulsifier, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water. The face cream of the above formula was prepared according to a conventional method for preparing cosmetics.
- This example provides an anti-aging or immunomodulatory emulsion, comprising components in mass percentage: 0.4-0.6% of Dendrobium officinale stock solution rich in oligosaccharides, 1.3-1.5% of stearic acid, 0.08-0.12% of cetyl alcohol, 1.7-1.9% of 2-ethyl alcohol cetyl stearate, 0.1-0.3% of isopropyl myristate, 0.9-1.1% of 2-hexyl-1-decanol, 7-8% of liquid paraffin, 2.5-3.5% of glycerol, 7-9% of propylene glycol, 0.08-0.12% of triethanolamine, 0.3-0.4% of a carboxyvinyl polymer, 1.5-2.5% of Arlacel 165, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water; The emulsion of the above formula was prepared according to a conventional method for preparing cosmetics.
- This example provides an anti-aging or immunomodulatory toner, comprising components in mass percentage: 1-10% of Dendrobium officinale stock solution rich in oligosaccharides, 0.3-0.4% of sodium polyacrylate, 3.5-4.5% of glycerol, 2-3% of 1,3-butanediol, 0.4-0.6% of vitamin B5, 0.4-0.6% of arbutin, 0.04-0.06% of EDTA-Na2, and the balance of deionized water; the method for preparing the toning lotion is as follows: the sodium polyacrylate was dissolved in water, stirred to fully swelling, then the remaining ingredients were added, and continued to stirring; then the Dendrobium officinale stock solution rich in oligosaccharides was added thereto, the mixture was stirred, and then deionized water was added to a constant volume to obtain the toner.
- A preferred solution is as follows: 0.35 g of sodium polyacrylate was dissolved in 70 mL of water, stirred to fully swelling, then the remaining ingredients were added, and continued to stirring; then 10% of the Dendrobium officinale stock solution rich in oligosaccharides obtained in Example 1 was added thereto, the mixture was stirred uniformly, and then deionized water was added to 100 mL and packed.
- This example provides an anti-aging or immunomodulatory repair cream, comprising components in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and the balance of deionized water.
- The method for preparing the repair cream is as follows: the carbomer was taken in an appropriate amount of deionized water, the mixture was stirred uniformly, let stand overnight to fully swelling, then glycerin was added, and the pH value was adjusted with triethanolamine to increase the viscosity of the gel matrix to obtain a carbomer gel; the Dendrobium officinale stock solution rich in oligosaccharides, propylene glycol and deionized water were mixed evenly, then the carbomer gel, essential oil and ethyl p-hydrobenzoate were added thereto, the resulting mixture was stirred until uniform and delicate, distilled water was added to a sufficient amount, and the mixture was grinded evenly to obtain a repair cream.
- A preferred solution is as follows: 6 g of glycerin, 1.5 g of carbomer, 1.5 g of triethanolamine, 6 g of propylene glycol, 0.2 g of ethyl p-hydrobenzoate, 10% of Dendrobium officinale stock solution rich in oligosaccharide obtained in Example 1, and an appropriate amount of deionized water were added to a total weight of 100 g. The preparation method is as follows: the carbomer was taken in an appropriate amount of deionized water, the mixture was stirred uniformly, let stand overnight to fully swelling, then glycerin was added, and the pH value was adjusted with triethanolamine to increase the viscosity of the gel matrix to obtain a carbomer gel; a prescription amount of tanshinone extract, propylene glycol and deionized water were mixed evenly, then the carbomer gel, 0.5% of an essential oil and ethyl p-hydrobenzoate were added thereto, the resulting mixture was stirred until uniform and delicate, distilled water was added to a sufficient amount, and the mixture was grinded evenly to obtain a repair cream.
- The above are only preferred embodiments of the present disclosure, and are not intended to be used to limit the present disclosure in any form. Any simple amendments, equivalent changes and modifications made to the above embodiments based on the technical essence of the present disclosure still fall within the scope of the technical solutions of the present disclosure.
Group | Sample well (µl) | Positive control well (µl) | Inhibitor control well (µl) | Background blank well (µl) |
Sample to be tested | 1-90 | - | - | - |
|
10 | 10 | 10 | - |
Inhibitor | - | - | 2 | - |
Protease buffer solution | Diluted to 100 | 90 | 88 | 100 |
Claims (16)
- A Dendrobium officinale oligosaccharide, comprising 3-9 glycoside residues and a glucose residue at a non-reducing end.
- The Dendrobium officinale oligosaccharide according to claim 1, wherein the Dendrobium officinale oligosaccharide comprises 6 glycoside residues.
- The Dendrobium officinale oligosaccharide according to claim 1, wherein the glycoside residue comprises a galactose residue, a mannose residue and a glucose residue.
- The Dendrobium officinale oligosaccharide according to claim 4, wherein a molar ratio of the galactose residue, the mannose residue and the glucose residue is (3-2) : (2-1) : (2-1).
- The Dendrobium officinale oligosaccharide according to claim 5, wherein a molar ratio of the galactose residue, the mannose residue and the glucose residue is 2 : 1 : 1.
- A Dendrobium officinale oligosaccharide derivative, wherein the Dendrobium officinale oligosaccharide derivative is generated by reacting the glucose residue of the Dendrobium officinale oligosaccharide according to any one of claims 1-6 with a hydrophobic residue, and the hydrophobic residue comprises any one of linear or branched C1-C18 alkyl, C1-C18 alkyl carboxylic acid, C1-C18 alkyl amine, C1-C18 aryl alkyl and C1-C18 alkyl amide, or
the hydrophobic residue comprises any one of benzoyl, phenylacetyl and phenylpropionyl. - Use of the Dendrobium officinale oligosaccharide according to any one of claims 1-6 or the Dendrobium officinale oligosaccharide derivative according to claim 7 in preparation of anti-aging or immunomodulatory products.
- The use according to claim 8, wherein the products comprises medicines, foods, formulations and cosmetics.
- The use according to claim 9, wherein a type of the cosmetics comprises a face cream, an emulsion, a toning lotion or a repair cream.
- A method for extracting the Dendrobium officinale oligosaccharide according to any one of claims 1-6, comprising:1) preparation of a Dendrobium officinale powder: drying a stem of Dendrobium officinale, then smashing and sieving to obtain a Dendrobium officinale powder;2) preparation of a water extract of Dendrobium officinale: mixing the Dendrobium officinale powder with water, subjecting to a boiling water bath for one or more times, and then merging water extracts to obtain a water extract of Dendrobium officinale;3) preparation of a concentrated water extract of Dendrobium officinale: centrifuging the water extract of Dendrobium officinale, and then concentrating under reduced pressure to obtain a concentrated water extract of Dendrobium officinale;4) preparation of a redissolving liquid: adding ethanol to the concentrated water extract of Dendrobium officinale, precipitating, centrifuging and then discarding a supernatant to obtain a precipitate; adding water to the obtained precipitate for redissolving to obtain a redissolving liquid;5) preparation of an aqueous solution of Dendrobium officinale oligosaccharide: deproteinizing the redissolving liquid, and freeze-drying to obtain a crude polysaccharide of Dendrobium officinale; adding water to dissolve the crude polysaccharide of Dendrobium officinale, then adding cellulase for a reaction, followed by inactivating and centrifuging, and discarding a precipitate to obtain an aqueous solution of Dendrobium officinale oligosaccharide;6) preparation of the Dendrobium officinale oligosaccharide: purifying the aqueous solution of Dendrobium officinale oligosaccharide to obtain the Dendrobium officinale oligosaccharide.
- The method according to claim 11, wherein,in step 1), a temperature for the drying is 50-60°C; a moisture mass content of the stem of Dendrobium officinale after the drying is less than 6%; a mesh number of the sieving is 20-40 meshes;in step 2), the Dendrobium officinale powder and water are mixed in a mass-volume ratio of 1 : (50-80) g/mL; the boiling water bath is performed for 2-3 times; a time for each boiling water bath is 1-2 h;in step 3), the centrifugation is conducted under conditions of 3000-4000 rpm/min, 8-12 min and room temperature; the concentration under reduced pressure is conducted under conditions of a rotary evaporation method, an ethanol recycling temperature of less than 50°C and a pressure of 0.7 Pa-0.9 Pa; a material-liquid mass-volume ratio of the concentrated water extract of Dendrobium officinale is 1 : (5-10) g/mL.
- The method according to claim 11, wherein,in step 4), the addition of ethanol to the concentrated water extract of Dendrobium officinale and the precipitation are specifically conducted as follows: adding ethanol with a volume concentration of 95% to the concentrated water extract of Dendrobium officinale until an alcohol concentration of a mixture is 70%-80% in volume percentage, and then precipitating overnight;the centrifugation is conducted under conditions of 3500-4500 rpm, 18-22 min and room temperature; a weight-volume ratio of the precipitate and water for the redissolving is 1 : (4-6) g/mL;in step 5), the deproteinization of the redissolving liquid is conducted by a Sevage method;a temperature for the freeze-drying is 45°C;the addition of water to dissolve the crude polysaccharide of Dendrobium officinale is conducted as follows: adding water to the crude polysaccharide of Dendrobium officinale for dissolving until 4.5-5.5 mg/mL;an added amount of the cellulase is 2%-4% of a weight of the crude polysaccharide of Dendrobium officinale;after adding the cellulase, the reaction is conducted under a reaction temperature of 55-65°C for a reaction time of 2 h-4 h;the inactivation is conducted by boiling for 25-35 min;the centrifugation is conducted under conditions of 3500-4500 rpm, 15-25 min and room temperature;an oligosaccharide content in the aqueous solution of Dendrobium officinale oligosaccharide is greater than 80%;in step 6), the purification is conducted by passing through a G75 gel column; a purity of the Dendrobium officinale oligosaccharide is 99.86%.
- A method for preparing the Dendrobium officinale oligosaccharide derivative according to claim 7, comprising:1) reducing a fatty acid into a fatty alcohol;2) glycosylating the fatty alcohol with the Dendrobium officinale oligosaccharide to obtain the Dendrobium officinale oligosaccharide derivative.
- The method according to claim 14, wherein in step 1), a reaction process of the reduction of a fatty acid into a fatty alcohol is as follows: mixing 9-11 mmol of the fatty acid, 18-22 mmol of NaBH4, 38-42 mmol of AlCl3, 25-29 ml of THF and 2-4 ml of MeOH for a reaction, and the reaction is conducted under a temperature of 95-105°C for a time of 7.5-8.5 h with a yield of 88-92%;
in step 2), a reaction process of the glycosylation is as follows: mixing the alcohol and the saccharide in a molar ratio of 1 : (8-10), and then using cetyl ammonium bromide as a catalyst for catalyzation, and the reaction is conducted under a temperature of 110-115°C for a time of 2.5-3.5 h with a yield of 78-82%. - An anti-aging or immunomodulatory product, wherein the anti-aging or immunomodulatory product is a face cream, an emulsion, a toning lotion or a repair cream;the face cream comprises in mass percentage: 0.4-0.6% of a Dendrobium officinale stock solution rich in oligosaccharides, 7.5-8.5% of stearic acid, 1.5-2.5% of C16 alcohol, 1.5-2.5% of self-emulsifying monoglyceride, 1.5-2.5% of hydrogenated lanolin, 11-13% of liquid paraffin, 6-8% of glycerin, 1-2% of an emulsifier, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water;the emulsion comprises in mass percentage: 0.4-0.6% of a Dendrobium officinale stock solution rich in oligosaccharides, 1.3-1.5% of stearic acid, 0.08-0.12% of cetyl alcohol, 1.7-1.9% of 2-ethyl alcohol cetyl stearate, 0.1-0.3% of isopropyl myristate, 0.9-1.1% of 2-hexyl-1-decanol, 7-8% of liquid paraffin, 2.5-3.5% of glycerol, 7-9% of propylene glycol, 0.08-0.12% of triethanolamine, 0.3-0.4% of a carboxyvinyl polymer, 1.5-2.5% of Arlacel 165, 0.1-0.3% of a preservative, 0.1-0.3% of an essence, and the balance of water;the toning lotion comprises in mass percentage: 1-10% of a Dendrobium officinale stock solution rich in oligosaccharides, 0.3-0.4% of sodium polyacrylate, 3.5-4.5% of glycerol, 2-3% of 1,3-butanediol, 0.4-0.6% of vitamin B5, 0.4-0.6% of arbutin, 0.04-0.06% of EDTA-Na2, and the balance of deionized water;the repair cream comprises in mass percentage: 5-7% of glycerin, 1.4-1.6% of carbomer, 1.4-1.6% of triethanolamine, 5.5-6.5% of propylene glycol, 0.15-0.25% of ethyl p-hydrobenzoate, 9-11% of a Dendrobium officinale stock solution rich in oligosaccharides, 0.4-0.6% of an essential oil, and the balance of deionized water.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110247117.XA CN113004432B (en) | 2021-03-05 | 2021-03-05 | Dendrobium officinale oligosaccharide, dendrobium officinale oligosaccharide derivative and preparation method and application thereof |
PCT/CN2021/129570 WO2022183763A1 (en) | 2021-03-05 | 2021-11-09 | Dendrobium officinale oligosaccharide and derivative thereof, and preparation methods therefor and applications thereof |
Publications (3)
Publication Number | Publication Date |
---|---|
EP4082519A1 EP4082519A1 (en) | 2022-11-02 |
EP4082519A9 true EP4082519A9 (en) | 2023-01-04 |
EP4082519A4 EP4082519A4 (en) | 2023-03-15 |
Family
ID=76407366
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP21876726.7A Pending EP4082519A4 (en) | 2021-03-05 | 2021-11-09 | Dendrobium officinale oligosaccharide and derivative thereof, and preparation methods therefor and applications thereof |
Country Status (6)
Country | Link |
---|---|
US (1) | US20230257484A1 (en) |
EP (1) | EP4082519A4 (en) |
JP (2) | JP2023528104A (en) |
KR (1) | KR20220131532A (en) |
CN (1) | CN113004432B (en) |
WO (1) | WO2022183763A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113004432B (en) * | 2021-03-05 | 2022-02-25 | 中国科学院昆明植物研究所 | Dendrobium officinale oligosaccharide, dendrobium officinale oligosaccharide derivative and preparation method and application thereof |
CN114478578B (en) * | 2021-12-24 | 2024-03-29 | 上海中医药大学 | Specific bioluminescence probe substrate for measuring carboxylesterase 1 and preparation method and application thereof |
CN114796245B (en) * | 2022-04-29 | 2023-11-10 | 上海中医药大学 | New application of dendrobium oligosaccharides |
CN114853824B (en) * | 2022-04-29 | 2024-07-09 | 上海中医药大学 | Preparation method of dendrobe oligosaccharide |
CN116024286A (en) * | 2022-11-28 | 2023-04-28 | 浙江农林大学 | Method for preparing ultralow molecular weight dendrobium oligosaccharide by using enzyme method and application thereof |
CN116656758B (en) * | 2023-06-26 | 2024-03-22 | 上海植纳生物科技有限公司 | Dendrobium oligosaccharide and fresh dendrobium juice as well as preparation methods and applications thereof |
CN117106832B (en) * | 2023-08-28 | 2024-03-08 | 东莞巨微新材料科技有限公司 | Dendrobium officinale polysaccharide extract with high and low molecular weight as well as preparation method and application thereof |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060251739A1 (en) * | 2005-05-04 | 2006-11-09 | National Yang-Ming University | Composition and method for treating autoimmune disease and mucosal disorder |
CN101716283A (en) * | 2009-11-20 | 2010-06-02 | 合肥工业大学 | Method for constructing dendrobium officinale polysaccharide fingerprinting |
CN103113483B (en) * | 2013-01-24 | 2015-05-20 | 北京航空航天大学 | Method for extracting various active ingredients from dendrobium officinale |
CN107267574B (en) * | 2017-06-30 | 2020-03-31 | 广东国方医药科技有限公司 | Dendrobium officinale polysaccharide fragment and extraction method thereof |
CN109295131B (en) * | 2017-12-04 | 2021-09-24 | 合肥工业大学 | Receptor positioning solid-phase enzymolysis preparation method of dendrobe active oligosaccharide |
CN108477612B (en) * | 2018-02-06 | 2021-07-30 | 刘利勇 | Dendrobium nutrition powder containing dendrobium officinale purified extract and preparation method thereof |
CN108635300A (en) * | 2018-07-19 | 2018-10-12 | 南京润斛堂生物科技有限公司 | A kind of cosmetics containing small molecule dendrobium polysaccharide and preparation method and application |
CN109232759A (en) * | 2018-09-19 | 2019-01-18 | 北京明弘科贸有限责任公司 | A kind of preparation process and its application of dendrobium nobile micromolecular polysaccharide extracting solution |
CN109535269A (en) * | 2018-09-26 | 2019-03-29 | 北京明弘科贸有限责任公司 | A kind of preparation process and its application of dendrobium nobile micromolecular polysaccharide extracting solution |
US11474100B2 (en) * | 2019-05-14 | 2022-10-18 | Hong Kong Baptist University | Chromophore-labeled oligosaccharide markers and methods of use thereof |
CN110128564B (en) * | 2019-06-06 | 2020-01-07 | 杭州寿而健健康产品有限公司 | Extraction method of micromolecule dendrobium officinale polysaccharide |
CN113004432B (en) * | 2021-03-05 | 2022-02-25 | 中国科学院昆明植物研究所 | Dendrobium officinale oligosaccharide, dendrobium officinale oligosaccharide derivative and preparation method and application thereof |
-
2021
- 2021-03-05 CN CN202110247117.XA patent/CN113004432B/en active Active
- 2021-11-09 WO PCT/CN2021/129570 patent/WO2022183763A1/en unknown
- 2021-11-09 US US17/788,422 patent/US20230257484A1/en active Pending
- 2021-11-09 KR KR1020227028738A patent/KR20220131532A/en active Search and Examination
- 2021-11-09 JP JP2022523441A patent/JP2023528104A/en active Pending
- 2021-11-09 EP EP21876726.7A patent/EP4082519A4/en active Pending
-
2024
- 2024-03-15 JP JP2024041539A patent/JP2024073584A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2022183763A1 (en) | 2022-09-09 |
KR20220131532A (en) | 2022-09-28 |
JP2024073584A (en) | 2024-05-29 |
EP4082519A1 (en) | 2022-11-02 |
CN113004432A (en) | 2021-06-22 |
US20230257484A1 (en) | 2023-08-17 |
JP2023528104A (en) | 2023-07-04 |
EP4082519A4 (en) | 2023-03-15 |
CN113004432B (en) | 2022-02-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP4082519A9 (en) | Dendrobium officinale oligosaccharide and derivative thereof, and preparation methods therefor and applications thereof | |
US20110236513A1 (en) | Substances capable of potentiating laminin 5 productivity in epidermal cells and their use | |
US20120178706A1 (en) | Method for preparing a centella asiatica extract rich in madecassoside and in terminoloside | |
EP1859834B1 (en) | Anti-inflammatory agent | |
KR100825450B1 (en) | Skin anti-wrinkle cosmetics composition containing Forsythiae Fruit extract | |
EP2432891B1 (en) | Methods for preparing a fermented ginseng concentrate or powder | |
KR20150100288A (en) | Cosmetic composition comprising the extract of crude drug fermentation using the black yeast | |
CN113350233A (en) | Anti-aging composition and preparation method and application thereof | |
KR101736916B1 (en) | Composition for improving atopy dermatitis using phthalide derivative | |
WO2024007901A1 (en) | Method for preparing oxyresveratrol | |
EP3750923A1 (en) | Separated saposhnikovia divaricata polysaccharide and use thereof | |
EP3501529B1 (en) | Method for preparing an extract of chrysanthemum morifolium with an effect of treating skin diseases, extract of chrysanthemum morifolium with an effect of treating skin diseases and pharmaceutical composition containing the extract | |
CN112386643A (en) | Application of Chinese violet extract in preparation of anti-aging composition | |
EP4349844A1 (en) | Novel phenylpropanoid compound | |
KR102654331B1 (en) | Preparation and application of a fermentation composition with anti-photoaging,calming,cooling effects | |
KR100680845B1 (en) | Magnolan extraction method from the flower of magnolia species and cosmetic compositions using magnolan | |
KR20180124443A (en) | Cosmetic composition for enhancing skin barrier containing extract of Tremella fuciformis fruiting body | |
WO2020203933A1 (en) | Antiaging agent, antioxidant, antiinflammatory agent and whitening agent, and cosmetic | |
KR100513430B1 (en) | Cosmetic composition containing ginsan polysaccharide extracted from Panax ginseng | |
CN112546107A (en) | Use of bergamot fermented juice for preparing composition for improving skin aging | |
TWI836834B (en) | Use of gentiana scabra extract for preparing composition for scalp health care | |
TWI834368B (en) | Uses of white bayberry extract for resisting aging or reducing fat | |
CN117414320A (en) | Preparation method and application of sweet tea extract | |
KR20160081161A (en) | Skin external composition for moisturizing or whitening the skin comprising compound K and acetic acid 16-hydroxy-octadeca-9,17-diene-12,14-diynyl ester | |
KR20160081165A (en) | Skin external composition for moisturizing or whitening the skin comprising compound K and picrionoside A |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20220411 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: BEIJING DR PLANT BIOTECHNOLOY CO., LTD. Owner name: KUNMING INSTITUTE OF BOTANY, CHINESE ACADEMY OF SCIENCES |
|
RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: BEIJING DR PLANT BIOTECHNOLOGY CO., LTD. Owner name: KUNMING INSTITUTE OF BOTANY, CHINESE ACADEMY OF SCIENCES |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20230214 |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: A61K 31/715 20060101ALI20230208BHEP Ipc: A61K 8/60 20060101ALI20230208BHEP Ipc: A61K 8/73 20060101AFI20230208BHEP |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20230912 |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) |